Guest Stars Chris Gethard as Himself Rich Sommer as Steven Charleston Rich Sommer as Himself Zach Cherry as Himself Jason Mantzoukas as Himself D'Arcy Carden as Herself Ben Schwartz as Himself Lea Thompson as Herself Paul Scheer as Himself Haley Joel Osment as Himself Janet Varney as Herself Will Hines as Himself Jon Gabrus as Himself J.D. Walsh as Himself Jackie Michele Johnson as Herself Shannon O'Neill as Herself Riley Soloner as Himself Griffin McElroy as Himself Craig Shemin as Himself Travis McElroy as Himself Justin McElroy as Himself Josh Gondelman as Himself Keiko Agena as Herself Tami Sagher as Herself Alan Sepinwall as Himself Jackie Jennings as Herself